Top 20 Times Talk Shows Hosts Made Celebrities Uncomfortable

Jane Fonda and co-star Robert Redford appeared on “Megyn Kelly Today” in 2017 to promote their new Netflix film “Our Souls at Night.” The pair are basically Hollywood legends, and conversation turned to their decades-long friendship and how they met. In the midst of this, Kelly complimented Fonda on aging “beautifully and with strength,” to which the audience applauded in agreement. However, Kelly then asked Fonda about having had plastic surgery. This clearly struck a sour note with the guest, who promptly turned the conversation back to the new film. Many felt it was a tactless and sudden way to change the subject on Kelly’s part, and Fonda was not having it. If looks could kill…

Former New York Jets quarterback Joe Namath had a short-lived talk show in 1969. One of his guests was boxing legend Muhammad Ali. The interview started with sports talk. But Ali, who was rather religious, became visibly uncomfortable when fellow guest, actor George Segal, began to talk about nude scenes in his latest film. Though Segal was the one responsible for the initial discomfort, Namath didn’t do much to help once Ali voiced his disdain for the topic. He kept questioning him, trying to force him to speak on a topic he had no interest in, and the tension was apparent. Eventually, co-host Dick Schaap changed the subject – but it took way too long.

When Ellen DeGeneres interviewed South Korean boy band BTS in 2017, their legion of fans was beyond thrilled, but they probably didn’t expect things to take this weird turn. Before the screaming, crying “BTS Army” in the audience, DeGeneres asked typical questions (using an interpreter) about their songs and supporters. She then threw in an awkward question: have they ever hooked up with any of their fans? After some translating, member V shouted a very distinct “no.” One uncomfortable pause later, the subject was thankfully changed. She was probably just trying to be funny, the whole thing arguably felt inappropriate, and we’re guessing the band members would’ve preferred to keep talking about their work instead.

Unfortunately for celebrities, interviews don’t always go as discussed beforehand, especially when attempts at comedy are made at their expense. In 2007, Paris Hilton was sentenced to 45 days in jail. This was of course publicized, but the star obviously didn’t want to talk about it. She appeared on “Late Show with David Letterman” with the intention of promoting and discussing her new perfume and projects. Letterman, however, had different ideas and began to extensively question her about her time in jail – and her friend Nicole Richie’s. He also had questions about the food there, for some reason. Despite her repeated short answers and claims that it was a traumatizing experience she had no interest in discussing, Letterman did not let up.

In 1993, Oprah Winfrey interviewed the King of Pop in a televised special titled “Michael Jackson Talks…to Oprah.” It was an era in which it really seemed that Oprah could do no wrong. But it turns out that she too could create awkward moments. Winfrey asked Jackson a variety of questions, and she was very thorough. Everything from the pop star’s childhood, popular rumors about him, and his romantic life were discussed. It was when getting into the latter topic that the host suddenly asked the singer about his level of sexual experience. Jackson seemed timidly taken aback and uncomfortable. He responded explaining that it was too personal a topic for him to discuss on such a platform.

Unfortunately, this isn’t the only time in this list that you’ll get “creepy” vibes. In 1995, Letterman interviewed a then up-and-coming Claire Danes. The conversation began with talk of astrological signs, which soon turned to the teenage Danes’ age at the time. Letterman appeared shocked and creepily disappointed, claimed he was nervous, and used this as a laughable moment that shouldn’t fly. He then questioned her about her boyfriend, but with a tone and demeanor that gave off uncomfortable energy. Danes was gracious throughout, but giggled nervously and at one point, she had her arms crossed in apparent discomfort. We can only imagine how uncomfortable it all made her.

Mexican actor Gael García Bernal appeared on “Jimmy Kimmel Live” in 2017 to promote the animated film “Coco.” The movie took inspiration from Día de los Muertos, or Day of the Dead, a holiday devoted to honoring and celebrating the departed. Kimmel asked Bernal about the Mexican holiday, which the latter graciously elaborated despite Kimmel’s almost childish interruptions. Bernal notably explained that an altar is set up with photographs of the departed to which offerings are made. Kimmel then tried to make jokes, but they’re more insensitive than funny. This can’t have been an easy conversation for the actor to get through, and we were uncomfortable with him. Still, he handled it very well.

Letterman was another host that could come off as sheltered when interviewing non-American guests, as is the case here. When the host interviewed Indian actress Aishwarya Rai Bachchan, his line of questioning immediately went to her culture. He questioned her as though she was from Narnia, either feigning or actually displaying ignorance. He poked fun at her for living with her parents, spoke of her worldwide fame while maintaining his lack of knowing who she is and creepily questioned her on her modeling career. To her credit, the actress was quick-witted and put the host in his place, despite her obvious discomfort shown in giggles and staredowns.

In 2002, Milla Jovovich appeared on France’s “Tout le Monde en Parle.” The guest had a translator, and the co-hosts talked about her in the third person in between questions. The tension seemed to begin a couple of minutes into the interview, as Jokovich was being interrupted and was understandably not having it. While she started out jovial and all smiles, things shifted dramatically during a segment in which Thierry Ardisson recounted her life and career from childhood. Everything seemed to be going smoothly until he mentioned the time when her father was arrested for insurance fraud. Jovovich admitted this to be true, then, visibly shaken, knocked her water glass off the table and angrily stormed off – yikes.

In 2010, Jay Leno had Sofía Vergara on his late night show, and the results were cringe-worthy. At one point, Leno put up Vergara’s vacation pictures. When the slide changed from a bikini shot, he insisted they go back to it. Sadly, things didn’t get better from there. The host then grilled her about her weight – which she obviously and understandably disliked. It was enough to make everyone – Vergara included – uneasy. It should also be noted that fellow guest Gordon Ramsay did nothing to make Vergara comfortable either. In fact, it was quite the opposite, as he behaved in an extremely inappropriate manner throughout the interview, something for which many have since called him out.

Taylor Swift has appeared on “Ellen” a number of times, but there were a few moments where she clearly wished she was elsewhere. DeGeneres would often ask Swift about her love life, which we know has gotten pretty old. In one particularly unsettling instance, she kept insisting that Swift had dated Zac Efron, despite the latter’s insistence that she had not. To make matters worse, the host then started going through a slideshow of the singer and various men. Anyone paying attention could tell Swift just wanted it to stop – especially because she eventually blatantly said so. Yet DeGeneres egged her on for far longer than necessary. The interaction hasn’t gotten easier to watch, and it keeps aging badly with each passing year.

In the mid-’90s, David Letterman interviewed Uma Thurman on “Late Show”, and it started out normally, with Dave making his usual light-hearted jokes. Yet things got gradually uncomfortable, as Letterman seemed to be attempting to flirt with Thurman. He speaks of her upcoming film, yet makes a shift into asking her the ages of the men she’s dated, slipping his own age into the mix. Uma, in turn, tries to change the subject while nervously laughing. He tops it off with complimenting her ears and calling her a “lovely piece of work.”

It’s hard to tell if this next one is a joke or a serious intellectual lapse. Even the guest appears confused. Kimmel was interviewing Katherine Langford from “13 Reasons Why,” who is an actress from Australia. The questioning started the usual way, but then the host asked the actress where she learned to speak English - that is, what he called “regular English,” or what they speak in America. She handled it with grace, yet the question was clearly greatly flawed. Perhaps the unease could have been prevented had Kimmel rephrased his question, and asked about accents instead. Or he could have acknowledged that he misspoke, which would have saved him from the verbal flub or failed wisecrack, whatever it may have been.

Back in 2015, Jimmy Kimmel received heat from the online gaming community after claiming to not understand the point of Let’s Plays and live streaming. To understand better, Kimmel met with YouTubers Markiplier and MissesMae, but didn’t exactly come with an open mind. Markiplier, trying to be his normal kind self, explained how being an influential gaming figure gives him the chance to make a difference, but Kimmel seemed more concerned with giving distasteful punchlines than listening. Seeing that the current approach was going nowhere, MissesMae opted to show how her parents reacted to virtual reality, thinking it might open Jimmy’s eyes. Nnnnnnnnnope. Then, after a quick foray into another game, it seemed like Markiplier and MissesMae couldn’t get out of there fast enough

In an interview with Joaquin Phoenix, Jimmy Kimmel brought up Joaquin Phoenix’s childhood break-dancing hobby. Phoenix seemed taken aback, perhaps not expecting the subject to come up. Kimmel pressed on, however, with Phoenix answering his questions - albeit visibly vexed while doing so; Phoenix even told him it wasn’t something to laugh about. To pour salt on the already sensitive wound, Kimmel surprised Phoenix with some “bonus” footage from “Joker,” which made the actor seem like kind of a diva. This led to a very uncomfortable Phoenix suddenly being made to apologize for his behavior on set. We can only assume he was really happy to see this interview come to a close.

In an interview with Angelina Jolie, David Letterman’s questions became increasingly… mmmm let’s say invasive, and she was clearly struggling to maintain her composure. He almost immediately commented on her “smelling nice,” and brought up her relationship status. She hesitated with her words, as Letterman pressed her for more answers. It became clear that Jolie was not enjoying herself during this interview. We’ve seen some of Letterman’s questionable behavior towards his female guests before on this list and we’ll see it again. And unfortunately, this cringey Angelina Jolie interview was no exception.

This one is extra cringy. During his “Graham Norton's Big Chat Live” segment of Comic Relief’s Red Nose Day telethon event in 2017, the host zeroed in on Delevingne when the topic of the “mile-high club” arose. He didn’t quite ask her if she’d done it on a plane before, but rather stated it. She immediately appeared embarrassed, and mentioned her father being in the crowd. Norton acknowledged this, yet pursued the line of questioning, brushing the dad issue aside in the quest for comedy gold. Delevingne doesn’t have such a great reputation as an interviewee, but it’s hard not to take her side on this one.

In 1995, Jay Leno spoke with Judith Light, of “Who’s the Boss?” fame. Things started off awkwardly, and to be honest, we can’t see an interview like this being allowed to take place today. The host immediately brought up a prior interview, in which they discussed a film where Light appeared nude. He then seemed to constantly be looking to raise the topic of her onscreen nudity. This somehow led to Light showing Leno how cable-tv nude shoots work, as he got way too close to her. He then held her hands behind her back and unbuttoned her shirt. She asked to go to commercial, clearly crying out for help, with fellow guest David Spade even showing obvious discomfort.

Fallon is a big fan of Pink Floyd, and was understandably excited to be interviewing Roger Waters on “Late Night.” The subject inevitably turned to Syd Barrett, a former member of the band who left and was rumored to have suffered from some serious mental health issues, namely schizophrenia. Waters was noticeably emotional when discussing the late Barrett, and took on a serious tone. Fallon then laughingly brought up a story about Barrett interrupting a Pink Floyd recording, referring to him as “a bald man with a toothbrush in his mouth”. Waters cleared up the story, making sure to tell Fallon that it wasn’t a funny tale, and that the entire situation was very sad.

In 1998, David Letterman talked to Jennifer Aniston at the height of her “Friends” fame. The interview started out normally, with typical questions and such. It then took a bit of a sudden weird turn, as Letterman asked for forgiveness, then leaned in ridiculously close to Aniston and took a strand of her hair in his mouth. (She was thankfully handed a napkin to clean it off). He then claimed she scared him, as she let out a slight yell when he was performing his inappropriate action. Just… bizarre. When the interview continued, Aniston was visibly nervous and stumbling over her words from that point forward.